Lewis Acid Catalyzed Intermolecular Olefin Hydroamination: Scope, Limitation, and Mechanism | Zendy

Cheng Xiaojuan | Zendy; Xia Yuanzhi | Zendy; Wei Hua | Zendy; Xu Bin | Zendy; Zhang Chongguang | Zendy; Li Yahong | Zendy; Qian Guimin | Zendy; Zhang Xiaohua | Zendy; Li Kai | Zendy; Li Wu | Zendy

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Lewis Acid Catalyzed Intermolecular Olefin Hydroamination: Scope, Limitation, and Mechanism

Author(s) -

Cheng Xiaojuan,

Xia Yuanzhi,

Wei Hua,

Xu Bin,

Zhang Chongguang,

Li Yahong,

Qian Guimin,

Zhang Xiaohua,

Li Kai,

Li Wu

Publication year - 2008

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200701080

Subject(s) - hydroamination , chemistry , carbocation , lewis acids and bases , catalysis , olefin fiber , norbornene , intermolecular force , cationic polymerization , organic chemistry , lewis acid catalysis , allylamine , copolymer , molecule , polyelectrolyte , polymer

Intermolecular olefin hydroamination was studied by various Lewis acids. The results of ZrCl 4 , FeCl 3 , BiCl 3 , and AlCl 3 catalyzed reactions of norbornene with aromatic amines were compared, and BiCl 3 was found to be the most effective catalyst to give high yields for various amines, whereas ZrCl 4 could promote the reactions at relatively low temperatures. The FeCl 3 catalyzed reactions were the most chemoselective and excellent yields could be achieved for certain amines by using AlCl 3 . A carbocation mechanism was proposed, and the controllable syntheses of allylamine and tetrahydroquinoline from isoprene and 2,5‐dichloroaniline were achieved by application of this mechanism. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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